IP Library › Granted Patent US 8,114,899
Granted Patent B2
US 8,114,899 · App. 12/360,535 · Granted Feb 14, 2012

2H- or 3H-benzo[e]indazol-1-yl carbamate derivatives, the preparation and therapeutic use thereof

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,114,899
App. No.
12/360,535
Granted
Feb 14, 2012
Kind
B2
Abstract

Compounds corresponding to the formula (I) as defined in the disclosure, as well as methods for making such compounds, intermediates employed in such methods, pharmaceutical compositions containing the compounds of the invention, and methods of treatment using them.

Claims (103)

1. A compound selected from the group consisting of:

7-Fluoro-2-(4-fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Fluoro-2-(4-fluorophenyl)-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-(pyridin-4-yl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydro-chloride;

7-Chloro-3-(pyridin-4-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

8-Methoxy-3-(pyridin-4-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

2-(4-Methylphenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-dimethylcarbamate;

2-(4-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

2-(3-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl morpholine-4-carboxylate;

2-(3-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-dimethylcarbamate;

2-(3-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

2-(3-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl pyrrolidine-1-carboxylate;

2-(3-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate;

2-Phenyl-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-phenyl-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

2-(3-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N-methyl-N-phenylcarbamate;

2-(2-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

2-Ethyl-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

2-Ethyl-4,5-dihydro-2H-benzo[e]indazol-1-yl N-methyl-N-phenylcarbamate;

2-(2,2′,2″-Trifluoroethyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N-methyl-N-phenylcarbamate;

2-(4-Fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

2-(4-Fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate;

2-(4-Fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N-methyl-N-phenylcarbamate;

2-(4-Fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl pyrrolidine-1-carboxylate;

2-(4-Fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl piperidine-1-carboxylate;

2-(4-Fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl morpholine-4-carboxylate;

2-(4-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-dimethylcarbamate;

2-(4-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate;

2-(4-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N-methyl-N-phenylcarbamate;

2-(4-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl pyrrolidine-1-carboxylate;

2-(4-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl piperidine-1-carboxylate;

2-(4-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl morpholine-4-carboxylate;

2-(4-Chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl 4-methylpiperazine-1-carboxylate;

2-(4-Fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-dimethylcarbamate;

2-(4-Fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl 4-methylpiperazine-1-carboxylate;

2-Phenyl-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-dimethylcarbamate;

2-Phenyl-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate;

2-Phenyl-4,5-dihydro-2H-benzo[e]indazol-1-yl N-methyl-N-phenylcarbamate;

2-Phenyl-4,5-dihydro-2H-benzo[e]indazol-1-yl pyrrolidine-1-carboxylate;

7-Chloro-2-(4-fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

2-(4-Fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N-methyl-N-propylcarbamate;

2-(3-Chloro-4-methylphenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

2-(3-Chloro-4-fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

1 7-Chloro-2-(3-chloro-4-methylphenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-(2,4-difluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate:

2-(Pyridin-4-yl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

7-Chloro-2-(pyridin-2-yl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Methoxy-2-(4-fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Bromo-2-(4-fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-(3-chloro-4-fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-methyl-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

2-(3-Chlorophenyl)-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

2-(4-Fluorophenyl)-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

2-(4-Fluorophenyl)-2H-benzo[e]indazol-1-yl N-methyl-N-propylcarbamate;

2-(3-Chloro-4-fluorophenyl)-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

2-(3-Chloro-4-methylphenyl)-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-(4-fluorophenyl)-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-(3-chloro-4-fluorophenyl)-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-(3-chloro-4-methylphenyl)-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-(2,4-difluorophenyl)-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Methoxy-3-(pyridin-4-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

7-Methyl-3-(pyridin-4-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

7-Chloro-3-(pyridin-3-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

7-Chloro-2-(pyridin-3-yl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

7-Fluoro-2-(pyridin-4-yl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

7-Fluoro-3-(pyridin-4-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

7-Chloro-3-(4-fluorophenyl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-3-(pyridin-2-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

7-Chloro-2-(3-fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-3-(3-fluorophenyl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Bromo-2-(pyridin-4-yl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

7-Bromo-3-(pyridin-4-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

7-Chloro-3-(4-methylphenyl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-(4-methylphenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-(2-fluorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-3-(4-chlorophenyl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-(4-chlorophenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-2-(4-methoxyphenyl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-3-(4-methoxyphenyl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-3-(3-fluorophenyl)-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate;

7-Chloro-3-(pyridin-4-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N-methyl-N-phenylcarbamate;

7-Chloro-2-(pyridin-4-yl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate;

7-Chloro-4,5-dihydro-3-(pyridin-4-yl)-3H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate hydrochloride;

6-Methoxy-3-(pyridin-4-yl)-4,5-di hydro-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride;

7-Chloro-3-(pyridin-4-yl)-3H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate hydrochloride;

7-Chloro-2-(pyridin-4-yl)-4,5-dihydro-2H-benzo[e]indazol-1-yl piperidine-1-carboxylate hydrochloride;

7-Chloro-3-(pyridin-4-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl piperidine-1-carboxylate hydrochloride;

7-Chloro-2-(pyridin-3-yl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate hydrochloride;

7-Chloro-3-(pyridin-3-yl)-4,5-di hydro-3H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate hydrochloride;

7-Chloro-3-(pyridin-4-yl)-4,5-di hydro-3H-benzo[e]indazol-1-yl N,N-diisopropylthiocarbamate hydrochloride;

7-Chloro-3-(pyridin-4-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl cis-2,6-dimethylpiperidine-1-carboxylate hydrochloride;

7-Chloro-2-(pyridin-4-yl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N-methyl-N-(tert-butyl)carbamate hydrochloride;

7-Chloro-3-(pyridin-3-yl)-3H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate hydrochloride;

7-Chloro-3-(pyridin-2-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate;

7-Fluoro-3-(pyridin-4-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate hydrochloride;

7-Chloro-3-(pyrimidin-2-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate;

7-Chloro-2-(pyrazin-2-yl)-4,5-dihydro-2H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate;

7-Fluoro-3-(pyridin-4-yl)-3H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate hydrochloride;

7-Chloro-3-(pyridin-2-yl)-3H-benzo[e]indazol-1-yl N,N-diisopropylcarbamate;

7-Chloro-3-(pyridin-4-yl)-4,5-dihydro-3H-benzo[e]indazol-1-yl N-methyl-N-(tert-butyl)carbamate hydrochloride;

7-Chloro-3-(pyridin-4-yl)-3H-benzo[e]indazol-1-yl N,N-diethylcarbamate hydrochloride; and

7-Chloro-3-(pyridin-4-yl)-3H-benzo[e]indazol-1-yl N-methyl-N-phenylcarbamate hydro-chloride.

2. A pharmaceutical composition comprising a compound according to claim 1 or a pharmaceutically acceptable salt thereof or a hydrate or a solvate thereof in combination with at least one pharmaceutically acceptable excipient.

Assignments (2)
CHANGE OF NAME Recorded Aug 13, 2012
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 028775/0284 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 12, 2011
From: DUBOIS, LAURENT; EVANNO, YANNICK; MALOIZEL, CHRISTIAN; SEVRIN, MIREILLE
To: SANOFI-AVENTIS
Reel/Frame 026885/0803 →